16495-13-9

Basic information

• Product Name: (S)-(+)-Benzyl glycidyl ether
• Synonyms: (s)-o-benzylglycidol;(S)-(+)-2-(BENZYLOXYMETHYL)OXIRANE;(S)-(+)-1-BENZYLOXY-2,3-EPOXYPROPANE;(S)-1-BENZYLOXY-2,3-EPOXYPROPANE;(S)-(+)-BENZYL GLYCIDYL ETHER;(S)-BENZYL GLYCIDYL ETHER;(S)-BENZYLOXYMETHYL-OXIRANE;(+)-BENZYL (S)-GLYCIDYL ETHER
• CAS NO: 16495-13-9
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.2
• EINECS: -0
• Product Categories: chiral;CHIRAL COMPOUNDS;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound
• Mol File: 16495-13-9.mol
• Article Data: 59

Chemical Properties

• Boiling Point: 130 °C (0.1 mmHg)
• Flash Point: >110°C
• Appearance: Colorless to light yellow liquid
• Density: 1.072 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.517
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Ethanol
• BRN: 5246495
• CAS DataBase Reference: (S)-(+)-Benzyl glycidyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-Benzyl glycidyl ether(16495-13-9)
• EPA Substance Registry System: (S)-(+)-Benzyl glycidyl ether(16495-13-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: TX2860030
• Hazardous Substances Data: 16495-13-9(Hazardous Substances Data)

Usage

Description

(S)-(+)-Benzyl glycidyl ether, also known as (S)-(+)-Glycidyl benzyl ether, is an aryl glycidyl ether that is colorless to light yellow in appearance. It is a valuable compound in the field of organic chemistry due to its ability to undergo stereospecific cyclizations, leading to the formation of 3-chromanols or tetrahydrobenzo[c]oxepin-4-ols. This enantiomerically pure compound has been synthesized with a 30%ee (enantiomeric excess) along with (R)-3-benzyloxypropane-1,2-diol with 40%ee, through its resolution using whole cells of Bacillus alcalophilus.

Uses

1. Used in Pharmaceutical Synthesis:
(S)-(+)-Benzyl glycidyl ether is used as a reactant in the synthesis of (+)-Discodermolide, a natural product with potential pharmaceutical applications. It serves as a key intermediate in the production of this compound, highlighting its importance in the development of new drugs.
2. Used in Total Asymmetric Synthesis:
(S)-(+)-Benzyl glycidyl ether may be employed for the total asymmetric synthesis of (+)-gigantecin, another biologically active compound with potential applications in the pharmaceutical industry. Its use in this process demonstrates its versatility and utility in the synthesis of complex organic molecules.
3. Used in Organic Chemistry Research:
As an aryl glycidyl ether, (S)-(+)-Benzyl glycidyl ether is used in various research applications to study the stereochemistry and reactivity of these types of compounds. Its ability to undergo stereospecific cyclizations makes it a valuable tool for understanding the underlying mechanisms and developing new synthetic strategies in organic chemistry.

Safety Profile

Mutation data reported. Whenheated to decomposition it emits acrid smoke andirritating vapors.

InChI:InChI=1/C10H12O2/c1-2-4-9(5-3-1)6-11-7-10-8-12-10/h1-5,10H,6-8H2/t10-/m1/s1

Upstream product

• 16495-12-8 (S)-Benzyl-(3-benzoyloxy-2-p-tosyloxy-propyl)-ether 
• 14593-43-2 benzyl allyl ether 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 23214-66-6 (R)-3-(benzyloxy)-2-hydroxypropyl 4-methylbenzene sulfonate 
• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 
• 62061-70-5 (S)-1-benzyloxy-2-bromo-2-propanol 
• 100-39-0 benzyl bromide 
• 78906-15-7 tert-butyldimethylsilyl (S)-glycidyl ether 
• 128495-88-5 (R)-2-acetoxy-1-chloro-3-benzyloxy-2-propanol 
• 112497-11-7 (R)-1-Benzyloxy-3-p-tolylsulfanyl-propan-2-ol 
• 137709-60-5 (S)-1-benzyloxy-3-bromo-2-propanol 
• 151715-97-8 (R)-2-butanoyl-1-phenylmethyl-3-chloro-1,2-propanediol 
• 97808-00-9 (S)-(-)-trimethyl<2-hydroxy-3-(benzyloxy)propyl>ammonium iodide 
• 57044-25-4 (R)-oxiranemethanol 

Downstream Products

• 125782-68-5 (S)-1-Benzyloxy-3-(5-hydroxymethyl-furan-2-yl)-propan-2-ol 
• 85758-01-6 (R)-5-Benzyloxy-4-hydroxy-2-p-tolyl-pentanenitrile 
• 112497-12-8 (S)-1-Benzyloxy-3-[1,3]dithian-2-yl-propan-2-ol 
• 145308-75-4 (S)-1-benzyloxy-4-decyn-2-ol 
• 130052-47-0 (R)-1-benzyloxy-2-hydroxyhexadecane 
• 116127-33-4 5-Benzyloxymethyl-3-(4-methyl-pent-3-enyl)-dihydro-furan-2-one 
• 130291-41-7 1,7-bis(benzyloxy)-4-benzenesulfonyl-(2R,6R)-heptanediol 
• 81309-78-6 (R)-5-Benzyloxy-2-(3,4-dimethoxy-phenyl)-4-hydroxy-pentanenitrile 
• 139242-76-5 (2S)-1-(Phenylmethoxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentanol 
• 150620-97-6 (S)-1-O-Benzylnonane-1,2-diol 
• 130052-46-9 (2'R)-1-O-(2'-methoxyhexadecyl)-3-O-benzyl-sn-glycerol 
• 130052-40-3 (2'S)-1-O-(2'-methoxyhexadecyl)-3-O-benzyl-sn-glycerol 
• 117039-90-4 (2S)-1-benzyloxy-2-butanol 
• 145229-56-7 (2R,6S)-1,7-Bis-benzyloxy-hept-3-yne-2,6-diol 

Relevant articles and documents

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Stereoselective total synthesis of (?)-galantinic acid and 1-deoxy-5-hydroxysphingolipids via prins cyclization

The stereoselective total synthesis of (?)-galantinic acid 1 and 1-deoxy-5-hydroxysphingolipids 4 is described via Prins cyclization protocol followed by reductive ring opening sequence of substituted pyrenol derivative 6. The target molecules were synthesized using a common synthetic intermediate epoxide 5. Besides, we also proposed synthetic pathways to achieve other structural analogues using common intermediates.

Improving the activity and enantioselectivity of PvEH1, a Phaseolus vulgaris epoxide hydrolase, for o-methylphenyl glycidyl ether by multiple site-directed mutagenesis on the basis of rational design

Substrate spectrum assay exhibited that PvEH1, which is an epoxide hydrolase from P. vulgaris, had the highest specific activity and enantiomeric ratio (E) for racemic o-methylphenyl glycidyl ether (rac-1) among tested aryl glycidyl ethers (1–5). To produce (R)-1 via kinetic resolution of rac-1 efficiently, the catalytic properties of PvEH1 were further improved on the basis of rational design. Firstly, the seven single-site variants of PvEH1-encoding gene (pveh1) were PCR-amplified as designed, and expressed in E. coli BL21(DE3). Among all expressed single-site mutants, PvEH1L105I and PvEH1V106I had the highest specific activities of 17.6 and 16.4 U/mg protein, respectively, while PvEH1L196D had an enhanced E value of 9.2. Secondly, to combine their respective merits, one triple-site variant, pveh1L105I/V106I/L196D, was also amplified, and expressed. The specific activity, E value, and catalytic efficiency of PvEH1L105I/V106I/L196D were 23.1 U/mg, 10.9, and 6.65 mM?1 s?1, respectively, which were 2.0-, 1.8- and 2.4-fold higher than those of wild-type PvEH1. The source of PvEH1L105I/V106I/L196D with enhanced E value for rac-1 was preliminarily analyzed by molecular docking simulation. Finally, the scale-up kinetic resolution of 100 mM rac-1 was conducted using 5 mg wet cells/mL E. coli/pveh1L105I/V106I/L196D at 25 °C for 1.5 h, producing (R)-1 with 95.0% ees, 32.1% yield and 3.52 g/L/h space-time yield.